Isopropyl iodide → HCID 69021376, compound

HRID 2052933Notes

Reaction equation

HRID 2052933 reaction equation
N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.[OH:12][CH:13]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)/[CH:14]=[CH:15]/[C@H:16]1[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[N:17]1[CH2:23][C:24]#[C:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].IC(C)C>CC(C)=O.CCOC(C)=O>[CH:3]([O:30][C:29](=[O:31])[CH2:28][CH2:27][CH2:26][C:25]#[C:24][CH2:23][N:17]1[C:18](=[O:22])[CH2:19][CH2:20][CH2:21][C@@H:16]1/[CH:15]=[CH:14]/[CH:13]([OH:12])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11222437HCID 11222437, compound

Product 1

HCID 69021376HCID 69021376, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (15 μL, 0.10 mmol) was added to a solution of 7-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-hept-5-ynoic acid (25 mg, 0.068 mmol) in acetone (0.68 mL) at rt. After 5 min, 2-iodopropane (34 μL, 0.34 mmol) was added. After 18 h at rt, the reaction mixture was diluted with EtOAc (25 mL) and washed with aqueous HCl (0.5 M, 10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient) afforded 13 mg (47%) of the title compound.

Workup

  1. waitAfter 18 h at rt
  2. washwashed with aqueous HCl (0.5 M, 10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-65856843b5f64cbf98a580a32f01d1ea
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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